Chessmaster is a great introduction to chess, but eventually he'll run out of lessons. Have you ever thought of getting him a diamond membership here so he'll have access to Chess Mentor? Many many more courses than Chessmaster and a greater variety of content. Lots of good videos as well and of course unlimited TT. Let me give you a link to 25 free ChessMentor courses that will give a great taste of what's available:
http://www.chess.com/blog/webmaster/free-chess-mentor-courses
Grandmaster probably isn't possible but everything else probably is depending on, of course, how hard he's willing to work (although Coach Heisman keeps emphasizing that chess has to be fun or you won't stick with it) and what his natural aptitude for the game is. If he's really putting 2 to 3 hours a day in, maybe you should get him involved in a scholastic chess program of some sort. Real chess is OTB tournaments; he'll find out in a hurry if he likes it. OTH of course you don't want to force him into doing anything. Hopefully a few of our wiser members will chime in on this thread as well. I do tend to be Captain Obvious , although I think he'll enjoy those CM courses.
My 13-year-old has been playing about a year. He's taken to the game and enjoys studying on Chessmaster, reading through chess books & magazines, and, of course, playing.
It's hard for me to get a gauge on his rating. Here he's something like 1100. On Chessmaster he's around 1000. On most rating exams he takes he ends up in the 1400 range.
Here's what I have him doing now: play a bunch, study Sillman's "Reasses" for up to 30 minutes a day, and sporadically study tactics, openings, and end games.
So he really has no formal chess training regimen. I'd like some advise on that. What should his training be like every day? I'd say he has anywhere from 2 to 3 free hours a day to devote to studying chess -- and he has the motivation.
Also, he's asking about how high his rating can eventually go. No idea. I doubt he'd ever be a GM since he didn't start moving pieces when he was 4 years old. I'm thinking maybe he can get up to Class A or Expert, but I don't know. Any thoughts on that as well?